78889-34-6Relevant articles and documents
Substitution of acetylenic groups for halogen in the quinonoid ring
Romanov,Ivanchikova,Moroz,Shvartsberg
, p. 1686 - 1689 (2005)
The bromine or iodine atom in the quinonoid ring devoid of+M substituent in the position neighboring to the halogen is replaced by acetylenic groups on treatment with CuI acetylides, prepared either beforehand or in situ, in a mixture of DMSO a
One-Pot Synthesis of 2- R-Naphtho[2,3- b]thiophene-4,9-diones via Cyclization of 2-(R-Ethynyl)-1,4-naphthoquinones with Na2S2O3
Baranov, Denis S.,Popov, Alexander A.,Nevostruev, Danil A.,Dmitriev, Alexey A.,Gatilov, Yurii V.,Kobeleva, Elena S.
, p. 11361 - 11369 (2021)
The concise and efficient one-pot synthesis of 2-R-naphtho[2,3-b]thiophene-4,9-diones from 2-bromo-1,4-naphthoquinone and alkynes has been developed. The reaction proceeds through the formation of 2-(R-ethynyl)-1,4-naphthoquinones, which undergo transformation with Na2S2O3 to 2-R-naphtho[2,3-b]thiophene-4,9-diones via C-H sulfuration, accompanied by the formation of the aromatic Bunte salt, followed by its air oxidation and 5-endo-dig cyclization. The protocol is characterized by simplicity, good tolerance for functional groups, relatively mild conditions, and commercially available starting compounds.
